US6342196B2ExpiredUtilityPatentIndex 66

Synthesis of hydrogen peroxide

Assignee: UNIV PITTSBURGHPriority: Jun 29, 1998Filed: Jun 29, 1998Granted: Jan 29, 2002

Est. expiryJun 29, 2018(expired)· nominal 20-yr term from priority

Inventors:BECKMAN ERIC J H ACIRC NCU DAN

C08G 65/007C07C 46/08C07C 235/16C07C 2603/24C07C 233/33C07C 69/157C01B 15/023C08G 65/2627C08G 65/3317

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Claims

Abstract

A method for synthesizing hydrogen peroxide comprises the steps of: synthesizing an analog of anthraquinone that is miscible or soluble in carbon dioxide; reacting the analog of anthraquinone with hydrogen in carbon dioxide to produce a corresponding analog of tetrahydroquinone; and reacting the analog of tetrahydroquinone with oxygen to produce the hydrogen peroxide and regenerate the analog of anthraquinone. A chemical compound having the formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently, the same or different, H, R C , or R S R C , wherein R S is a spacer group and R C is a fluoroalkyl group, a fluoroether group, a silicone group, an alkylene oxide group, a fluorinated acrylate group, or a phosphazine group, and wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is not H.

Claims

exact text as granted — not AI-modified

What is claimed is:

1. A method for synthesizing hydrogen peroxide, comprising the steps of:
synthesizing an analog of anthraquinone that is soluble in or miscible with carbon dioxide;
reacting the analog of anthraquinone with hydrogen in carbon dioxide to produce a corresponding tetrahydroquinone; and
reacting the tetrahydroquinone with oxygen to produce the hydrogen peroxide and regenerate the analog of anthraquinone.

2. The method of claim 1 further comprising the step of recycling the regenerated analog of anthraquinone.

3. The method of claim 1 wherein the step of synthesizing an analog of anthraquinone that is miscible in carbon dioxide comprises the step of attaching to anthraquinone at least one modifying group that is soluble in CO 2 .

4. The method of claim 1 wherein the analog of anthraquinone has the formula:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently H, R C or R S R C , wherein R S is a spacer group and R C is a fluoroalkyl group, a fluoroether group, a silicone group, an alkylene oxide group, a fluorinated acrylate group, or a phosphazine group, and wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is not H.

5. The method of claim 4 wherein the spacer group is an alkyl group, an amino group, an amido group, an alkyl ester group or an ester group.

6. The method of claim 5 wherein the spacer group is —NHCO—, —N(CH 3 )C(O)— or —CH 2 OCO—.

7. The method of claim 4 wherein molecular weight of the fluoroalkyl group, the fluoroether group, the silicone group or the alkylene oxide group is between approximately 50 and approximately 7500.

8. The method of claim 4 wherein molecular weight of the fluoroalkyl group, the fluoroether group, the silicone group or the alkylene oxide group is between approximately 500 and approximately 5000.

9. The method of claim 4 wherein molecular weight of the fluoroalkyl group, the fluoroether group, the silicone group or the alkylene oxide group is between approximately 500 and approximately 1500.

10. The method of claim 4 wherein the fluoroalkyl group has the formula:

—(CF 2 ) g —

wherein g is an integer and the fluoroalkyl group has a molecular weight between approximately 200 and approximately 7500.

11. The method of claim 4 wherein the fluoroether group has the formula:
wherein each of x, y and z is an integer greater than or equal to 0 and at least one of x, y and z is not equal to 0 and the fluoroether group has a molecular weight between approximately 200 and approximately 7500.

12. The method of claim 4 wherein the silicone group has the formula:
wherein R 9 and R 10 are, independently, H, an alkyl group, a fluoroalkyl group, an aryl group, an alkenyl group, and an alkoxyl group, wherein b is an integer and the silicone group has a molecular weight between approximately 200 and approximately 7500.

13. The method of claim 12 wherein R 9 or R 10 is a fluoroalkyl group.

14. The method of claim 4 wherein the alkylene oxide group has the formula:
wherein d is an integer and e is an integer and the alkylene oxide group has a molecular weight between approximately 200 and approximately 7500.

15. The method of claim 1 wherein operating pressure is no greater than 5000 psi.

16. The method of claim 1 wherein operating pressure is no greater than 3000 psi.

17. The method of claim 1 wherein operating pressure is no greater than 2500 psi.

18. The method of claim 1 wherein operating pressure is no greater than 1500 psi.

19. The method of claim 1 wherein the corresponding tetrahydraquinone is reacted with oxygen in carbon dioxide.

20. The method of claim 19 wherein the hydrogen peroxide is recovered via a liquid-liquid extraction between the carbon dioxide and an aqueous phase.

21. A method for synthesizing hydrogen peroxide, comprising the steps of:
synthesizing an analog of anthraquinone having the formula:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently, the same or different, H, R C , or R S R C , wherein R S is a spacer group and R C is a fluoroalkyl group, a fluoroether group, a silicone group, an alkylene oxide group, a fluorinated acrylate group, or a phosphazine group, and wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is not H;
reacting the analog of anthraquinone with hydrogen to produce a corresponding tetrahydroquinone having the formula;
reacting the tetrahydroquinone with oxygen to produce the hydrogen peroxide and regenerate the analog of anthraquinone, the analog of anthraquinone being liquid during the synthesis.

22. The method of claim 21 wherein the synthesis takes place without use of a solvent.

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